Three new cyathane diterpenoids named stercorins A-C (), including one with unusual 4,9--carbon skeleton, together with two new drimane sesquiterpenoids named stercorins D () and E () were isolated from the liquid cultures of the basidiomycete . Their structures were established by 1D and 2D NMR data in conjunction with HR-ESI-MS. All three cyathane diterpenoids showed neurotrophic activity in PC-12 cells at concentrations of 10 M. Compounds significantly suppressed LPS-induced NO production in culture medium in BV2 cells with the IC values of 1.64 M, 9.25 M and 8.71 M, respectively. Notably, Compound , possessing an uncommon medium-sized 9/7 ring system showed the most promising role in the prevention of two activities-associated neurodegenerative diseases.
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http://dx.doi.org/10.1080/14786419.2020.1739043 | DOI Listing |
J Am Chem Soc
September 2024
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
A powerful Pt-catalyzed asymmetric diboration/desymmetric double-allylboration cascade reaction has been developed for the construction of synthetically useful, densely functionalized hydrindanes with five stereocenters, including three quaternary ones, in good yields and excellent enantiomeric excess (ee) values within a single synthetic operation. A unified strategy utilizing this key tandem methodology enabled the concise asymmetric total synthesis of cyathane diterpene (-)-Cyathin B in 14 steps from commercially available starting materials, thereby demonstrating its remarkable potential in the synthesis of hydrindane-containing natural products and pharmaceuticals.
View Article and Find Full Text PDFNat Prod Res
December 2024
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, China.
Two previously undescribed natural cyathane diterpenoids Me-dentifragilin A () and Epi-neocyathin O (), and three known cyathane diterpenoids -, cyathin O, neocyathin P, and cyathin I, were isolated from the rice medium of the CBPFE A06. Their structures were established by NMR spectra, and HR-ESI-MS. Compounds - displayed encouraging neurotrophic activity in PC-12 cells at doses of 5 µM.
View Article and Find Full Text PDFMolecules
August 2023
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 3 Taicheng Road, Yangling 712100, China.
The culinary medicinal mushroom holds significant global esteem and has garnered heightened interest within increasingly ageing societies due to its pronounced neuroprotective and anti-neuroinflammatory properties. Within this study, two novel diterpenes, 16-carboxy-13--neoverrucosane () and Erinacine L (); three known xylosyl cyathane diterpenoids, Erinacine A (), Erinacine C (), and Erinacine F (); and four lanostane-type triterpenoids, and three cyclic dipeptides (-), in addition to orcinol (), were isolated from the rice-based cultivation medium of . Their structures were determined by NMR, HR-ESI-MS, ECD, and calculated NMR.
View Article and Find Full Text PDFJ Antibiot (Tokyo)
June 2023
Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University, Iksan, Korea.
During the search for natural antibiotics from fungal metabolites, a new cyathane diterpenoid, fragilicine A (1), and three known cyathane diterpenoids, erinacines I, A, and B (2-4) were isolated from the culture broth of Dentipellis fragilis. Chemical structures of 1-4 were determined by analyses of 1D- and 2D-NMR and MS data and by comparisons with data of those reported in the literature. These isolated compounds were assessed for their antimicrobial activities against Bacillus subtilis, B.
View Article and Find Full Text PDFActa Pharm Sin B
September 2021
State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.
Mushroom-derived cyathane-type diterpenes possess unusual chemical skeleton and diverse bioactivities. To efficiently supply bioactive cyathanes for deep studies and explore their structural diversity, synthesis of cyathane diterpenes in a geranylgeranyl pyrophosphate engineered is investigated. Aided by homologous analyses, one new unclustered FAD-dependent oxidase EriM accounting for the formation of allyl aldehyde and three new NADP(H)-dependent reductases in the biosynthesis of cyathanes are identified and elucidated.
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